Few artists have embodied the sound and ethos of their entire genre the way Miles Davis did with jazz. When Davis’ career began, even the shift from the uppity early 20th-century sounds of bebop to the laid-back tones of cool jazz was considered a highly controversial move, yet by the end of his life, he was leading his band into 30-plus-minute psychedelic freefalls, pushing the genre ever onwards into the future while taking inspiration from whatever styles suited his fancy. Even his most relaxed-sounding work bears all the creative energy of a true maverick, and his powerful visions of what jazz could be endure in their vividness even today.

As an emerging voice on Manhattan’s mid-’40s bebop scene, Davis originally distinguished himself with his smooth, minimal style of trumpet playing—ironic, given how bold his ventures into jazz would become. His first major stylistic shift came with his development of cool jazz, embodied most famously on the 1957 album Birth Of The Cool, a compilation of sessions dating back to 1949-50. But even this sound wouldn’t contain Davis for long—by the end of the ‘50s, he had become a firm collaborator with big-band arranger Gil Evans, recording a number of orchestral jazz masterpieces such as Porgy and Bess and Sketches of Spain, as well as the defining document of modal jazz (and possibly jazz in general), Kind of Blue.

From here, Davis would only push the limits of his craft even further, and the loose, hard-to-define post-bop sounds of albums like Miles Smiles and Nefertiti would eventually bloom into the electric, rock-fueled incantations of In a Silent Way and Bitches Brew, two albums that ushered Davis into the ‘70s completely unbeholden to any notions of traditionalism or boundaries. As Davis’ arrangements and performances became increasingly frenzied (see the amorphous funk of On The Corner or the free-flowing fusion of Agharta), his health started to decline as well, which resulted in a hiatus that lasted until the ‘80s, upon which Davis returned for a final string of records powered by synths and drum machines (including the rap-crossover Doo-Bop) before passing in 1991.

The mark that Davis has left on music is staggering. His reflections of jazz are both tender and enigmatic in equal measure, and tackling his entire career is no small feat. But to explore the music of Miles Davis is to understand the shifting state of culture in America, to see the ways in which our borders have materialized and dissolved as time has marched on, and to understand how the unleashed insanity of a later album like 1977’s Dark Magus can secretly be brewing under the stately calm of early work like Milestones all along. Davis’ career may be daunting, but the beauty of it is that there is no wrong place to start—no matter where one decides to pick up the thread, there are countless revelations to be found.